Synthesis and reduction of new sulfinimines with isobornane structure

Изместьев, Е. С.; Судариков, Д. В.; Рубцова, С. А.; Слепухин, П. А.; Кучин, А. В.

doi:10.1134/s1070428012110024

Cited by 11 publications

(6 citation statements)

References 8 publications

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“…The works [65][66][67][68] Neomenthanethiol 83 [68,69] and isobornanethiol 13 [68,[70][71][72] were also synthesized in good yields via isothiouronium salts 87 and 88, proceeding from alcohols 84 and 89 (Scheme 14). In addition to neomenthanethiol 83 and isobornanethiol 13, the authors of [68] prepared 4-caranethiol 91 and cis-myrtanethiol 92 using the same method.…”

Section: Synthesis From Alcohol Via Tosylates Halides Isothiouronium ...mentioning

confidence: 99%

Monoterpene Thiols: Synthesis and Modifications for Obtaining Biologically Active Substances

Sudarikov,

Nikitina,

Rollin

et al. 2023

IJMS

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Monoterpene thiols are one of the classes of natural flavors that impart the smell of citrus fruits, grape must and wine, black currants, and guava and are used as flavoring agents in the food and perfume industries. Synthetic monoterpene thiols have found an application in asymmetric synthesis as chiral auxiliaries, derivatizing agents, and ligands for metal complex catalysis and organocatalysts. Since monoterpenes and monoterpenoids are a renewable source, there are emerging trends to use monoterpene thiols as monomers for producing new types of green polymers. Monoterpene thioderivatives are also known to possess antioxidant, anticoagulant, antifungal, and antibacterial activity. The current review covers methods for the synthesis of acyclic, mono-, and bicyclic monoterpene thiols, as well as some investigations related to their usage for the preparation of the compounds with antimicrobial properties.

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Section: Synthesis From Alcohol Via Tosylates Halides Isothiouronium ...mentioning

confidence: 99%

Monoterpene Thiols: Synthesis and Modifications for Obtaining Biologically Active Substances

Sudarikov,

Nikitina,

Rollin

et al. 2023

IJMS

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“…Terpene thiols can be used as intermediates in organic synthesis to produce sulfochlorides, [15–17] sulfonamides, [18] sulfides, [4,8,9,19] disulfides, [5,20] sulfenimines and sulfinimines [7,21–25] . Chiral monoterpene hydroxythiols can also be used as chiral ligands or organocatalysts in asymmetric catalysis and as chiral auxiliaries in asymmetric synthesis [26–36] .…”

Section: Introductionmentioning

confidence: 99%

“…Chiral monoterpene hydroxythiols can also be used as chiral ligands or organocatalysts in asymmetric catalysis and as chiral auxiliaries in asymmetric synthesis [26–36] . Previously, we have developed methods for producing monoterpene menthane, [20,21] bornane, [22] pinane [37] and carane thiols [38] …”

Section: Introductionmentioning

confidence: 99%

Synthesis of Chiral CF₃‐Contaning Pinane‐Type Hydroxythiols

et al. 2021

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For the first time, the isomeric trifluoromethylated thioacetates have been synthesized in 37–52 % yields by nucleophilic addition of the Ruppert‐Prakash reagent (TMSCF3) to the corresponding thioacetates based on (1R)‐(−)‐myrtenal and (1S)‐(−)‐verbenone. Thioacetates have been transformed into the corresponding pinane thiols in 73–90 % yields. The structure and configuration of the resulting compounds have been determined.

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“…Thus, so far, the traditional methods available for sulfinamide synthesis from thiols require two or more synthetic steps and harsh reaction conditions, with significant limitations in the substrate scope [44, 61, 69, 70, 72, 73] . Besides these limitations, most of the methodologies for sulfinamide preparation, independently of the type of starting materials used, lead to the synthesis of N ‐functionalized sulfinamides, which often need to be subsequently deprotected [35, 74] to reveal the free ‐ NH 2 group.…”

Section: Introductionmentioning

confidence: 99%

Hydroxylamine‐Derived Reagent as a Dual Oxidant and Amino Group Donor for the Iron‐Catalyzed Preparation of Unprotected Sulfinamides from Thiols

2020

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An iron catalyzed reaction for the selective transformation of thiols (‐SH) to sulfinamides (‐SONH2) by a direct transfer of ‐O and free ‐NH2 groups has been developed. The reaction operates under mild conditions using a bench stable hydroxylamine derived reagent, exhibits broad functional group tolerance, is scalable and proceeds without the use of any precious metal catalyst or additional oxidant. This novel, practical reaction leads to the formation of two distinct new bonds (S=O and S−N) in a single step to chemoselectively form valuable, unprotected sulfinamide products. Preliminary mechanistic studies implicate the role of the alcoholic solvent as an oxygen atom donor.

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Synthesis and reduction of new sulfinimines with isobornane structure

Cited by 11 publications

References 8 publications

Monoterpene Thiols: Synthesis and Modifications for Obtaining Biologically Active Substances

Monoterpene Thiols: Synthesis and Modifications for Obtaining Biologically Active Substances

Synthesis of Chiral CF₃‐Contaning Pinane‐Type Hydroxythiols

Hydroxylamine‐Derived Reagent as a Dual Oxidant and Amino Group Donor for the Iron‐Catalyzed Preparation of Unprotected Sulfinamides from Thiols

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Synthesis and reduction of new sulfinimines with isobornane structure

Cited by 11 publications

References 8 publications

Monoterpene Thiols: Synthesis and Modifications for Obtaining Biologically Active Substances

Monoterpene Thiols: Synthesis and Modifications for Obtaining Biologically Active Substances

Synthesis of Chiral CF3‐Contaning Pinane‐Type Hydroxythiols

Hydroxylamine‐Derived Reagent as a Dual Oxidant and Amino Group Donor for the Iron‐Catalyzed Preparation of Unprotected Sulfinamides from Thiols

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Synthesis of Chiral CF₃‐Contaning Pinane‐Type Hydroxythiols